Annapolis Spring Sailboat Show

City Dock Annapolis, MD, United States

For 3 days at the City Dock in Historic Downtown Annapolis, almost 100 sailboats will be on display in the water and on land, including catamarans, mono-hulls, family cruisers, day sailors, and blue water sailboats. Because most sailboats are available for immediate sale, families can realize their dream of spending the summer on a new [...]

May Day in Annapolis

Downtown Annapolis, MD, United States

The beautiful historic city of Annapolis looks even more spectacular on May Day when homes and businesses decorate their doors with bouquets and baskets of fresh flowers. This years 60th Annual May Day Basket Competition will bring color and fragrance to the streets of Downtown Annapolis, and is not to be missed. Say hello to [...]

Maryland Avenue & State Circle Spring Festival

Maryland Avenue & State Circle Merchants Association 69 Maryland Ave, Annapolis, MD, United States

The brick paved sidewalks of Maryland Avenue & State Circle are home to some of the most historic buildings in all of Annapolis, with the past seeping out from each street and building. The shops you will discover while strolling this memorable location are full of charm, elegance and  style, and this years May Day [...]

First Sunday Arts Festival

First block of West and Calvert Streets Annapolis, MD, United States

Enjoy live entertainment while admiring the works of 100 local and regional artists as you stroll along the first block of West and Calvert Streets next to Whitmore parking garage. Local restaurants set up outside cafes that are perfect for people watching over an afternoon snack. This family friendly event has the benefit of free [...]

Class of 2019 Herndon Climb,

U.S. Naval Academy 121 Blake Road, Annapolis, MD, United States

As a tradition during Commissioning Week, the first-year plebes will climb the 21-foot obelisk to retrieve a white "dixie cup" hat on top of the monument and replace it with an upperclassman's hat.

Paint Annapolis

Around Annapolis Annapolis, MD, United States

There could not be a more beautiful city to paint than Annapolis, and the 5 day plein air Paint Annapolis competition will bring plein air painters from around the world to this historic city. Plein air means to paint outside, so the streets of Annapolis will be scattered with artists aiming to capture the atmosphere and [...]

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